(R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester

Base Information

• Chemical Name: (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester
• CAS No.: 153294-00-9
• Molecular Formula: C9H9ClO3
• Molecular Weight: 200.622
• Mol file: 153294-00-9.mol

Synonyms:methyl (R)-3-chloromandelate;(R)-(3-Chloro-phenyl)-hydroxy-acetic acid methyl ester;methyl (R)-2-(3-chlorophenyl)-2-hydroxyacetate;(R)-(-)-3-chloromandelic acid methyl ester;(R)-methyl 2-(3-chlorophenyl)-2-hydroxyacetate;(R)-methyl 3-chloromandelate;(R)-(-)-methyl 2-(3-chlorophenyl)-2-hydroxyacetate;

Chemical Property of (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester

Chemical Property:

• PSA: 46.53000
• LogP: 1.54640

Purity/Quality:

98% ^*data from raw suppliers

Methyl(R)-3-Chloromandelate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl (R)-3-Chloromandelate is an intermediate in the synthesis of Solabegron Hydrochloride (S676510). Solabegron Hydrochloride is a selective β3-adrenergic receptor agonist, that also produces Somatostatin (S676750). This drug is used for the treatment of irritable bowel syndrome.

Technology Process of (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester

There total 14 articles about (R)-Hydroxy-(3-chloro-phenyl)-acetic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.3%

methanol (67-56-1) + (R)-3-chloromandelic acid (16273-37-3,32222-43-8,52950-16-0,61008-98-8) → (R)-3-chloromandelic acid methyl ester (153294-00-9)

Guidance literature:

toluene-4-sulfonic acid; for 2h; Heating / reflux;

Reference yield: 95.0%

methanol (67-56-1) + (R)-(+)-2-hydroxy-2-(3-chlorophenyl)acetonitrile (122047-10-3) → (R)-3-chloromandelic acid methyl ester (153294-00-9)

Guidance literature:

methanol; (R)-(+)-2-hydroxy-2-(3-chlorophenyl)acetonitrile; With hydrogenchloride; at 80 ℃; for 6h;

With sodium hydrogencarbonate; In water; at 0 ℃; for 1h; pH=8.0;

Reference yield: 92.0%

methyl 3-chlorophenyldiazoacetate (264882-01-1) → (R)-3-chloromandelic acid methyl ester (153294-00-9)

Guidance literature:

With iron(II) chloride tetrahydrate; C₃₅H₃₀N₂O₂; sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; water; In chloroform; at 40 ℃; for 20h; optical yield given as %ee; Inert atmosphere;

DOI:10.1038/nchem.651

upstream raw materials:

methanol

(R)-3-chloromandelic acid

(R)-(+)-2-hydroxy-2-(3-chlorophenyl)acetonitrile

diazomethyl-trimethyl-silane

Downstream raw materials:

methyl (2R)-{[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)ethanoate

(R)-3-chloromandelamide

tert-butyl 2-((2R,5R,6R)-6-(3-chlorophenyl)-4-(cyclopropylmethyl)-3-oxo-5-((phenylsulfonyl)-1H-indol-2-yl)morpholin-2-yl)acetate

tert-butyl 2-((2S,5R,6R)-6-(3-chlorophenyl)-4-(cyclopropylmethyl)-3-oxo-5-((phenylsulfonyl)-1H-indol-2-yl)morpholin-2-yl)acetate